Coating compositions for the coating out of anionic mordant-acid dye layers



United States Patent 3,408,193 COATING COMPOSITIONS FOR THE COATING OUT OF ANIONIC MORDANT-ACID DYE LAYERS Wilfred L. Wolf and Clark Beckett, Rochester, N.Y., as-

signors to Eastman Kodak Company, Rochester, N.Y., a corporation of New Jersey No Drawing. Filed Dec. 16, 1964, Ser. No. 418,881 8 Claims. (Cl. 96-84) This invention relates to mordant-dye layers in which certain particular coating aids are employed in their composition.

Jones and Milton application Ser. No. 167,666, now

Patent No. 3,282,699 describes mordant-dye compositions for use as layers in photographic elements such as for filter layers or antihalation layers which compositions are composed of a basic mordant having recurring basic groups, an acid dye, a water permeable hydrophilic colloid binder and as the coating aid therein saponin. Saponin varies widely in purity and often contains material which desensitizes or has other derogatory elfects upon the silver halide emulsion with which it comes in contact. Therefore, it is desirable in photographic uses to use synthetic coating aids which have a uniform composition and are free of materials which might exert a derogatory effect on the photographic materials which they contact. In using the common coating aids such as of the anionic type in mordant-dye compositions high concentrations thereof are often needed to obtain satisfactory coatings. In addition these anionic coating aids tend to promote wandering of the dyes in the compositions into adjacent photographic emulsion layers resulting in desensitization of those layers.

The specification of application Ser. No. 167,666, filed J an. 22, 1962, describes photographic elements containing layers composed of basic mordant, acid dye and hydrophilic colloid and is incorporated herein by reference.

One object of our invention is to provide mordant-acid dye coating compositions which use a synthetic coating aid in the coating out of those compositions onto a support. Another object of our invention is to provide basic mordant-acid dye compositions containing coating aids which do not promote the wandering of the dyes into adjacent silver halide photographic emulsion layers or require use in high proportions as is the case with many of the coating aids commonly considered useful in coating out photographic layers. Other objects of our invention will appear herein,

We have found that basic mordant-acid dye coating compositions which contain as the coating aids therein salts of alkyl substituted or acyl substituted amino acids as described in U.S. Patents Nos. 3,133,816 and 3,142,568 and in US. application Ser. No. 225,108 give coatings of good uniformity. The disclosures of the patents (Nos. 3,133,816 and 3,142,568) and the application (No. 225,- 108) referred to are incorporated herein by reference. We have found that concentrations in the coating compositions of no more than of these coating aids based on the gelatin can be used with good results although greater amounts can be used if desired. We have found that coating aids of this type do not cause wandering of the dye into adjacent silver halide photographic emulsion layers, hence, desensitization of the emulsion layer is avoided. We have found that compositions in accordance with our invention are susceptible to coating out as layers at speeds of 50-500 feet per minute in coating operations in which hoppers of the type described in US. Patents Nos. 2,681,294 and 2,761,791 are used.

Patented Oct. 29, 1968 The following examples will illustrate our invention:

Example 1 Parts coating aid per Repellency Coating aid parts gelatin coating by wt. defects Triton-X 200 (p-tert-octylphenoxy ethoxy ethyl sulfonate) 7 High. Triton-X 200 10. 6 Fewer. Deriphat 151 (sodium N-coco-betaaminopropionate) 2 None.

Where coco represents a. mixture of high molecular weight hydrocarbon radlcals corresponding to those present in the esters in cocoanut oil.

Example 2 Two multilayer color films were prepared and coated as described in Example 16 of US. Patent No. 2,944,900 except that a yellow filter layer of the type described in Example 1 was used instead of the Carey Lea silver-blue light filter layer and a gelatin-basic mordant-magenta acid dye layer was coated between the green sensitive and red sensitive layers. In preparing one film an anionic coating aid was used in the mordant-dye layers and in the other a sodium salt of an alkyl aminopropionate as listed in Patent No. 3,133,816 was employed. The films were exposed on a sensitometer and were processed as described in Example 2 of U.S. Patent No. 2,944,900. The results obtained were as follows:

The invention has been described in considerable detail with particular reference to certain preferred embodiments thereof, but it will be understood that variations and modifications can be elfected within the spirit and scope of the invention as described hereinabove and as defined in the appended claims.

We claim:

1. A composition adapted to the coating out of layers for photographic products comprising in an aqueous system a hydrophilic colloid, a polymeric mordant having recurring basic groups, an acid dye and a coating aid selected from the group consisting of the compounds having the following general formulae:

ANH(CH COOM and AN[(CH ),,COOM] wherein A is selected from the group of aliphatic hydrocarbon radicals and aliphatic acyl radicals of 8-20 carbon atoms, x=1-2 and M is a cation which will contribute to the water solubility of the coating aid.

2. A photographic element having as a layer therein a mixture of a hydrophilic colloid, a polymeric mordant having recurring basic groups, an acid dye and .a coating 3 aid selected from the group consisting of the compounds having the following general formulae:

ANH(CH COOM AN (CH COOM]- wherein A is selected from the group of aliphatic hydrocarbon radicals and aliphatic acyl radicals of 8-20 carbon atoms, x=12 and M is a cation which will contribute to the water solubility of the coating aid.

3. A composition adapted to the coating out of layers for photographic products comprising in an aqueous system a hydrophilic colloid, a polymeric mordant having recurring basic groups, an acid dye and as the coating aid therein a compound having the formula:

RCON[ (CH COOM] 2 in which x=l2 and R is a radical having 11-17 carbon atoms and M is a cation contributing to water solubility of the coating aid.

4. A composition adapted to the coating out of layers for photographic products comprising in an aqueous system a hydrophilic colloid, a polymeric mordant having recurring basic groups, an acid dye and as the coating aid therein a compound having the formula:

RNHCHZCHZCOOX wherein R is an aliphatic hydrocarbon radical having from 8 to 20 carbon atoms and X is selected from the group consisting of hydrogen, an alkali metal, ammonium and an organic amine cation.

and

6. A composition adapted to the coating out of layers for photographic products comprising in an aqueous system a hydrophilic colloid, a polymeric mordant having recurring basic groups, an acid dye and as the coating aid therein sodium N-coco-beta-aminopropionate.

7. A composition adapted to the coating out of layers for photographic products comprising in an aqueous system gelatin as the hydrophilic colloid, poly-alpha-methylallyl-N-guanidyl-ketimine as the mordant, yellow sulfonated benzoXazole-pyrazolone dye and as the coating aid a compound selected from the group consisting of those having the following general formulae:

ANH(CH COOM and AN (CH COOM] 2 wherein A is selected from the group of aliphatic hydrocarbon radicals and aliphatic acyl radicals of 8-20 carbon atoms, x=12 and M is a cation which will contribute to the water solubility of the coating aid.

8. A composition adapted to the coating out of layers for photographic products comprising in an aqueous system gelatin as a hydrophilic colloid, poly-alpha-methylallyl-N-guanidylketimine as the mordant, yellow sulfonated benZoXaZole-pyrazolone as the acid dye and as the coating aid sodium N-coco-beta-aminopropionate.

References Cited UNITED STATES PATENTS 2,240,471 4/1941 Swan 96-109 XR 2,882,156 4/1959 Minsk 96-84 3,016,306 1/1962 Mader et a1. 96-84 XR 3,133,816 5/1964 Ben-Ezra 96-94 3,142,568 7/1964 Nottorf 96-87 3,282,699 11/ 1966 Jones et al. 96-84 3,306,749 2/ 1967 Knox et a1 96-94 NORMAN G. TORCHIN, Primary Examiner.

I. TRAVIS BROWN, Examiner.

R. H. SMITH, Assistant Examiner. 

1. A COMPOSITION ADAPTED TO THE COATING OUT OF LAYERS FOR PHOTOGRAPHIC PRODUCTS COMPRISING IN AN AQUEOUS SYSTEM A HYDROPHILIC COLLOID, A POLYMERIC MORDANT HAVING RECURRING BASIC GROUPS, AN ACID DYE AND A COATING AID SELECTED FROM THE GROUP CONSISTING OF THE COMPOUNDS HAVING THE FOLLOWING GENERAL FORMULAE:
 2. A PHOTOGRAPHIC ELEMENT HAVING AS A LAYER THEREIN A MIXTURE OF A HYDROPHILIC COLLOID, A POLYMERIC MORDANT HAVING RECURRING BASIC GROUPS, AN ACID DYE AND A COATING AID SELECTED FROM THE GROUP CONSISTING OF THE COMPOUNDS HAVING THE FOLLOWING GENERAL FORMULAE: 